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There are mirror images wherever you look as AC Milan host Tottenham Hotspur in the Champions League last 16 at the San Siro this evening.

Inconsistency, injuries and uncertainty over the managerial positions have made this something of a sliding doors tie for both sides. Few observers would have either as realistic challengers for a place in May's final in Istanbul yet Spurs fans might well recall that in 2019 it was a woefully out-of-form team struggling with injuries and uncertainty over their head coach that made it all the way to the decider in Madrid for a match they ultimately lost to Liverpool.

All told, though, neither team seems equipped enough to go deep into the tournament. Both struggled to exit their Champions League groups with just three wins apiece and have been toiling for consistency for most of the campaign and if Spurs 2019 provide the precedent for how a poor group campaign might not necessarily be the obstacle it would seem, there are other factors at play that suggest a repeat of those exploits are slim.

Milan's woes have been accentuated by a kind of injury crisis that would surely be rejected by the scriptwriters of Casualty for being too unrealistic. 

In the five month stretch from July 1 to the end of last year, Milan had racked up 700 days of absences with key contributors, such as Zlatan Ibrahimovic, Alessandro Florenzi, Mike Maignan, Simon Kjaer, Davide Calabria, Junior Messias, Alexis Saelemaekers, Ante Rebic and Theo Hernandez, all among the number of missing men.

Having been denuded some of his best players, Stefano Pioli's 4-2-3-1 system that worked so well last season has malfunctioned due to a combination of those absences, a lack of form and the failure of new signings – notably Charles de Ketelaare and Divock Origi – to click.

Milan ended a seven-game winless run across all competitions with a 1-0 Serie A victory against Torino last Friday that took them up to fifth place. Spurs, meanwhile, continued on their inconsistent way by following a win over Manchester City with resounding defeat at Leicester which kept them in their place just outside the Champions League places.

They, too, now find themselves in the midst of a mini-crisis having lost Hugo Lloris (knee), Rodrigo Bentancur (anterior cruciate ligament) and Yves Bissouma (ankle fracture) to long-term injuries all within the space of a week. 

The Herald:

Meanwhile, the run of poor form has ramped up the pressure on Pioli. Speculation in Italy suggests that should he fail to secure European football of any kind next season then the 57-year-old, who was given so much credit as Milan ended their 11-year wait for a Scudetto last May, might be looking for a new job.

Similar uncertainty surrounds the future of Antonio Conte, the Tottenham manager, just as it did with Mauricio Pochettino four years ago. The Italian has endured a difficult second season at Spurs, where results have not been as expected following an impressive end to the 2021/22 campaign when he helped steer Spurs to a Champions League place that had seemed unlikely at this stage last year. Conte has not had his troubles to seek this season. The death of his close friend Gian Piero Ventrone in October and concerns over his own health plus the fact that his Spurs contract is due to expire this summer has given weight to the belief that he will return to Italy this summer – despite the fact Tottenham have the option of a year's extension to his contract should they wish to trigger it.

More likely might be a return to the San Siro, where Conte was so successful at Milan's city rivals Inter, with reports in the Italian press stating that the 53-year-old is on a two-man shortlist to replace Pioli. Conte's time in the Tottenham job has had a peculiar sense of the impermanent about it with his public utterances often hinting that he will be off the first time a better offer comes along and Tottenham's January transfer activity did little dispel the idea that they might be holding funds back for a new man.